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Volumn 53, Issue 1, 1999, Pages 56-67

A comparative study of cyclization strategies applied to the synthesis of head-to-tail cyclic analogs of a viral epitope

Author keywords

Cyclic peptides; Epitope peptides; Foot and mouth disease virus; Solid phase mediated cyclization

Indexed keywords

CESIUM; CYCLOPEPTIDE; EPITOPE; MONOCLONAL ANTIBODY; VIRUS PROTEIN;

EID: 0342644832     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.1999.tb01617.x     Document Type: Article
Times cited : (16)

References (39)
  • 1
    • 84985653969 scopus 로고
    • Cyclic peptides: Past, present, and future
    • 1. Blout, E.R. (1981) Cyclic peptides: past, present, and future. Biopolymers 20, 1901-1912.
    • (1981) Biopolymers , vol.20 , pp. 1901-1912
    • Blout, E.R.1
  • 2
    • 0001447789 scopus 로고
    • The cyclic peptides: Structure, conformation, and function
    • (Neurath, H. & Hill, R.L., eds), Academic Press, New York
    • 2. Ovchinnikov, Y.A., Ivanov, V.T. (1982) The cyclic peptides: structure, conformation, and function. In The Proteins (Neurath, H. & Hill, R.L., eds), Academic Press, New York, pp. 307-642.
    • (1982) The Proteins , pp. 307-642
    • Ovchinnikov, Y.A.1    Ivanov, V.T.2
  • 3
    • 0020163940 scopus 로고
    • Conformation and biological activity of cyclic peptides
    • 3. Kessler, H. (1982) Conformation and biological activity of cyclic peptides. Angew. Chem. Int. Ed. Engl. 21, 512-523.
    • (1982) Angew. Chem. Int. Ed. Engl. , vol.21 , pp. 512-523
    • Kessler, H.1
  • 4
    • 0025336463 scopus 로고
    • Emerging approaches in the molecular design of receptor-selective ligands: Conformational, topographical and dynamic considerations
    • 4. Hruby, V.J., Al-Obeidi, F. & Kazmierski, W. (1990) Emerging approaches in the molecular design of receptor-selective ligands: conformational, topographical and dynamic considerations. Biochem. J. 268, 249-262.
    • (1990) Biochem. J. , vol.268 , pp. 249-262
    • Hruby, V.J.1    Al-Obeidi, F.2    Kazmierski, W.3
  • 5
    • 0026766974 scopus 로고
    • Constrained peptides: Models of bioactive peptides and protein substructures
    • 5. Rizo, J. & Gierasch, L.M. (1992) Constrained peptides: models of bioactive peptides and protein substructures. Annu. Rev. Biochem. 61, 387-418.
    • (1992) Annu. Rev. Biochem. , vol.61 , pp. 387-418
    • Rizo, J.1    Gierasch, L.M.2
  • 7
    • 0025029685 scopus 로고
    • Antigenic properties and protective capacity of a cyclic peptide corresponding to site A of influenza virus haemagglutinin
    • 7. Muller, S., Plaué, S., Samana, J.P., Valette, M., Briand, J.P. & Van Regenmortel, M.H.V. (1990) Antigenic properties and protective capacity of a cyclic peptide corresponding to site A of influenza virus haemagglutinin. Vaccine 8, 308-314.
    • (1990) Vaccine , vol.8 , pp. 308-314
    • Muller, S.1    Plaué, S.2    Samana, J.P.3    Valette, M.4    Briand, J.P.5    Van Regenmortel, M.H.V.6
  • 8
    • 0025729547 scopus 로고
    • Design of bioactive peptides based on antibody hypervariable region structures. Development of conformationally constrained and dimeric peptides with enhaced affinity
    • 8. Williams, W.V., Kieber-Emmons, T., Von Feldt, J., Greene, M.I. & Weiner, D.B. (1991) Design of bioactive peptides based on antibody hypervariable region structures. Development of conformationally constrained and dimeric peptides with enhaced affinity. J. Biol. Chem. 226, 5182-5190.
    • (1991) J. Biol. Chem. , vol.226 , pp. 5182-5190
    • Williams, W.V.1    Kieber-Emmons, T.2    Von Feldt, J.3    Greene, M.I.4    Weiner, D.B.5
  • 9
    • 0022454040 scopus 로고
    • Immunogenicity of loop-structured short synthetic peptides mimicking the antigenic site A of influenza virus haemagglutinin
    • 9. Schulze-Gahmen, U., Kenk, H.-D. & Beyreuther, K. (1986) Immunogenicity of loop-structured short synthetic peptides mimicking the antigenic site A of influenza virus haemagglutinin. Eur. J. Biochem. 159, 283-389.
    • (1986) Eur. J. Biochem. , vol.159 , pp. 283-389
    • Schulze-Gahmen, U.1    Kenk, H.-D.2    Beyreuther, K.3
  • 10
    • 0029019739 scopus 로고
    • Structure of major antigenic loop of foot-and-mouth disease virus complexed to anti-virus neutralizing antibody. Direct involvement of Arg-Gly-Asp in the interaction
    • 10. Verdaguer, N., Mateu, M.G., Andreu, D., Giralt, E., Domingo, E. & Fita, I. (1995) Structure of major antigenic loop of foot-and-mouth disease virus complexed to anti-virus neutralizing antibody. Direct involvement of Arg-Gly-Asp in the interaction. EMBO J. 14, 1690-1696.
    • (1995) EMBO J. , vol.14 , pp. 1690-1696
    • Verdaguer, N.1    Mateu, M.G.2    Andreu, D.3    Giralt, E.4    Domingo, E.5    Fita, I.6
  • 11
    • 0031963629 scopus 로고    scopus 로고
    • A similar pattern of interaction for different antibodies with a major antigenic site of foot-and-mouth disease virus: Implications for intratypic antigenic variation
    • 11. Verdaguer, N., Sevilla, N., Valero, M.L., Stuart, D., Brocchi, E., Andreu, D., Giralt, E., Domingo, E., Mateu, M.G. & Fita, I. (1998) A similar pattern of interaction for different antibodies with a major antigenic site of foot-and-mouth disease virus: implications for intratypic antigenic variation. J. Virol. 72, 739-748.
    • (1998) J. Virol. , vol.72 , pp. 739-748
    • Verdaguer, N.1    Sevilla, N.2    Valero, M.L.3    Stuart, D.4    Brocchi, E.5    Andreu, D.6    Giralt, E.7    Domingo, E.8    Mateu, M.G.9    Fita, I.10
  • 14
    • 0027216643 scopus 로고
    • Cyclic disulfide model of the major antigenic site of serotype-C foot-and-mouth disease virus
    • 14. Camarero, J.A., Andreu, D., Cairó, J.J., Mateu, M.G., Domingo, E. & Giralt, E. (1993) Cyclic disulfide model of the major antigenic site of serotype-C foot-and-mouth disease virus. FEBS Lett. 328, 159-164.
    • (1993) FEBS Lett. , vol.328 , pp. 159-164
    • Camarero, J.A.1    Andreu, D.2    Cairó, J.J.3    Mateu, M.G.4    Domingo, E.5    Giralt, E.6
  • 15
    • 0000842337 scopus 로고
    • Quantitative determination of D-and L-amino acids by reaction with tert-Butyloxycarbonyl-L-leucine N-hydroxysuccinimide ester and cromatographic separation as L,D and L,L dipeptides
    • 15. Mitchell, A.R., Kent, S.B.H., Chu, I.C. & Merrifield, R.B. (1978) Quantitative determination of D-and L-amino acids by reaction with tert-Butyloxycarbonyl-L-leucine N-hydroxysuccinimide ester and cromatographic separation as L,D and L,L dipeptides. Anal. Chem. 50, 637-640.
    • (1978) Anal. Chem. , vol.50 , pp. 637-640
    • Mitchell, A.R.1    Kent, S.B.H.2    Chu, I.C.3    Merrifield, R.B.4
  • 17
    • 0000066117 scopus 로고
    • Determination of D-amino acids by deuterium labelling and selected ion monitoring
    • 17. Liardon, R., Ledermann, S. & Ott, U. (1981) Determination of D-amino acids by deuterium labelling and selected ion monitoring. J. Chrom. 203, 385-395.
    • (1981) J. Chrom. , vol.203 , pp. 385-395
    • Liardon, R.1    Ledermann, S.2    Ott, U.3
  • 18
    • 0025957117 scopus 로고
    • Determination of the enantiomeric purity of synthetic peptides by gas chromatography-mass spectrometry
    • 18. Celma, C. & Giralt, E. (1991) Determination of the enantiomeric purity of synthetic peptides by gas chromatography-mass spectrometry. J. Chrom. 562, 447-458.
    • (1991) J. Chrom. , vol.562 , pp. 447-458
    • Celma, C.1    Giralt, E.2
  • 19
    • 33747866223 scopus 로고
    • The preparation of Merrifield-resíns through total esterification with cesium salts
    • 19. Gisin, B.F. (1973) The preparation of Merrifield-resíns through total esterification with cesium salts. Helv. Chim. Acta 56, 1476-1482.
    • (1973) Helv. Chim. Acta , vol.56 , pp. 1476-1482
    • Gisin, B.F.1
  • 20
    • 0001926444 scopus 로고
    • Solid-phase peptide synthesis
    • (Gross, E. & Meinhofer, J., eds), Academic Press, New York
    • 20. Barany, G., Merrifield, R.B. (1979) Solid-phase peptide synthesis. In The Peptides (Gross, E. & Meinhofer, J., eds), Vol. 2, pp. 1-284, Academic Press, New York.
    • (1979) The Peptides , vol.2 , pp. 1-284
    • Barany, G.1    Merrifield, R.B.2
  • 21
    • 0000281160 scopus 로고
    • Cyclohexyl esters as a new protecting group for aspartyl peptides to minimize aspartimide formation in acidic and basic treatments
    • 21. Tam, J.P., Wang, T., Riemen, M.W., Tjoeng, F. & Merrifield, R.B. (1979) Cyclohexyl esters as a new protecting group for aspartyl peptides to minimize aspartimide formation in acidic and basic treatments. Tetrahedron Lett. 42, 4033-4036.
    • (1979) Tetrahedron Lett. , vol.42 , pp. 4033-4036
    • Tam, J.P.1    Wang, T.2    Riemen, M.W.3    Tjoeng, F.4    Merrifield, R.B.5
  • 25
    • 0025730051 scopus 로고
    • Synthesis of cyclic peptides on solid support
    • 25. Rovero, P., Quartara, L. & Fabbri, G. (1991) Synthesis of cyclic peptides on solid support. Tetrahedron Lett. 32, 2639-2642.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 2639-2642
    • Rovero, P.1    Quartara, L.2    Fabbri, G.3
  • 26
    • 0026320903 scopus 로고
    • Solid phase synthesis of a cyclic peptide using Fmoc chemistry
    • 26. McMurray, J.S. (1991) Solid phase synthesis of a cyclic peptide using Fmoc chemistry. Tetrahedron Lett. 32, 7679-7682.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 7679-7682
    • McMurray, J.S.1
  • 27
    • 33845559580 scopus 로고
    • Chemistry of polymer-bound o-benzyne frequency of encounter between substituents on cross-linked polystyrenes
    • 27. Mazur, S. & Jayalekshmy, P. (1979) Chemistry of polymer-bound o-benzyne frequency of encounter between substituents on cross-linked polystyrenes. J. Am. Chem. Soc. 101, 677-683.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 677-683
    • Mazur, S.1    Jayalekshmy, P.2
  • 28
    • 0026565870 scopus 로고
    • Studies on antigenic variability of C strains of foot-and-mouth disease virus by means of synthetic peptides and monoclonal antibodies
    • 28. Carren̄o, C., Roig, X., Cairó, J.J., Camarero, J., Mateu, M.G., Domingo, E., Giralt, E. & Andreu, D. (1992) Studies on antigenic variability of C strains of foot-and-mouth disease virus by means of synthetic peptides and monoclonal antibodies. Int. J. Pept. Protein Res. 39, 41-47.
    • (1992) Int. J. Pept. Protein Res. , vol.39 , pp. 41-47
    • Carreno, C.1    Roig, X.2    Cairó, J.J.3    Camarero, J.4    Mateu, M.G.5    Domingo, E.6    Giralt, E.7    Andreu, D.8
  • 29
    • 33845557921 scopus 로고
    • Improved synthesis of 4-alkoxybenzyl alcohol resin
    • 29. Lu, G., Mojsov, S., Tam, J.P. & Merrifield, R.B. (1981) Improved synthesis of 4-alkoxybenzyl alcohol resin. J. Org. Chem. 46, 3433-3436.
    • (1981) J. Org. Chem. , vol.46 , pp. 3433-3436
    • Lu, G.1    Mojsov, S.2    Tam, J.P.3    Merrifield, R.B.4
  • 30
    • 0029329776 scopus 로고
    • Solution versus solid-phase cyclization strategies for large side chain lactam-bridged peptides: A comparative study
    • 30. Camarero, J.A., Cairó, J.J., Giralt, E. & Andreu, D. (1995) Solution versus solid-phase cyclization strategies for large side chain lactam-bridged peptides: a comparative study. J. Pept. Sci. 1, 241-250.
    • (1995) J. Pept. Sci. , vol.1 , pp. 241-250
    • Camarero, J.A.1    Cairó, J.J.2    Giralt, E.3    Andreu, D.4
  • 31
    • 0028475713 scopus 로고
    • Influence of solid support, solvent and coupling reagent on the head-to-tail cyclization of resin-bound peptide
    • 31. McMurray, J.S., Lewis, C.A. & Obeyesekere, N.U. (1994) Influence of solid support, solvent and coupling reagent on the head-to-tail cyclization of resin-bound peptide. Peptide Res. 7, 195-206.
    • (1994) Peptide Res. , vol.7 , pp. 195-206
    • McMurray, J.S.1    Lewis, C.A.2    Obeyesekere, N.U.3
  • 32
    • 0027406752 scopus 로고
    • A novel, convenient, three-dimensional orthogonal strategy for solid-phase synthesis of cyclic peptides
    • 32. Kates, S.A., Solé, N.A., Johnson, C.R., Hudson, D., Barany, G. & Albericio, F. (1993) A novel, convenient, three-dimensional orthogonal strategy for solid-phase synthesis of cyclic peptides. Tetrahedron Lett. 34, 1549-1552.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 1549-1552
    • Kates, S.A.1    Solé, N.A.2    Johnson, C.R.3    Hudson, D.4    Barany, G.5    Albericio, F.6
  • 33
    • 0014772602 scopus 로고
    • Color test for detection of free terminal amino groups in solid-phase synthesis of peptides
    • 33. Kaiser, E., Colescott, R.L., Bossinger, C.D. & Cook, P.I. (1970) Color test for detection of free terminal amino groups in solid-phase synthesis of peptides. Anal. Biochem. 4, 595-598.
    • (1970) Anal. Biochem. , vol.4 , pp. 595-598
    • Kaiser, E.1    Colescott, R.L.2    Bossinger, C.D.3    Cook, P.I.4
  • 34
    • 0040923731 scopus 로고
    • Formation of piperidides in peptides containing Asp-Gly during Fmoc synthesis, as identified by 2D NMR and tandem MS
    • (Maia, H.L.M., ed), Escom, Leiden
    • 34. Otto, H., Kaiser, D., Kempter, C., Jung, G. (1995) Formation of piperidides in peptides containing Asp-Gly during Fmoc synthesis, as identified by 2D NMR and tandem MS. In Peptides 1994. Proceedings of the Twenty-Third European Peptide Symposium (Maia, H.L.M., ed), Escom, Leiden, pp. 246-247.
    • (1995) Peptides 1994. Proceedings of the Twenty-Third European Peptide Symposium , pp. 246-247
    • Otto, H.1    Kaiser, D.2    Kempter, C.3    Jung, G.4
  • 36
    • 0030152676 scopus 로고    scopus 로고
    • A novel, convenient, three-dimensional orthogonal strategy for solid-phase synthesis of cyclic peptides
    • 36. Kates, S.A., Solé, N.A., Beyermann, M., Barany, G. & Albericio, F. (1996) A novel, convenient, three-dimensional orthogonal strategy for solid-phase synthesis of cyclic peptides. Peptide Res. 9, 106-113.
    • (1996) Peptide Res. , vol.9 , pp. 106-113
    • Kates, S.A.1    Solé, N.A.2    Beyermann, M.3    Barany, G.4    Albericio, F.5
  • 37
    • 0030061507 scopus 로고    scopus 로고
    • An approach to cyclic peptides libraries: Reducing epimerization in medium sized rings during solid phase synthesis
    • 37. Spatola, A.F., Darlak, K. & Romanovskis, P. (1996) An approach to cyclic peptides libraries: reducing epimerization in medium sized rings during solid phase synthesis. Tetrahedron Lett. 37. 591-594.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 591-594
    • Spatola, A.F.1    Darlak, K.2    Romanovskis, P.3
  • 39
    • 0029992878 scopus 로고    scopus 로고
    • Solid phase-mediated cyclization of head-to-tail peptides: Problems associated with side chain anchoring
    • 39. Valero, M.-L., Giralt, E. & Andreu, D. (1996) Solid phase-mediated cyclization of head-to-tail peptides: problems associated with side chain anchoring. Tetrahedron Lett. 37, 4229-4232.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 4229-4232
    • Valero, M.-L.1    Giralt, E.2    Andreu, D.3


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